Tampa Bay Brewing Co. is fantastic in Ybor City I always make a stop there for a beer and at least some fries (try the fries dipped in the curry sauce.) They have other beers besides whats on the menu written up on a chalk board in the corner to the right of the bar.
About 10 minutes away from there is Cigar City brewery which is a great production brewery. Very cool people and a great place to check out as they will usually have some beers on tap from Swamp Head here in Gainesville and Dunedin Brewery in Dunedin. You won't have to travel to try those.
In Orlando it's not quite that easy. Orlando Brewing Partners make some good beer but I haven't been too happy with most of them, decent but not great.
oh and lakeridge winery is an interesting experience if you are into that. picked up some of their muscadine juice last time I went, waiting on my pyment to finish still. I need to check out tampa bay brewing.
Tampa Bay Brewing and Cigar City are pretty close. Traffic is a nightmare though so don't do it during rush hour unless you go to Cigar City first.
Also, there is a Whole Foods and a Total Wine right in front of Cigar City, if they don't have bottles of something there you might be able to find them at one of those two places. The manager at Total Wine has hooked me up in the past with beers he had tucked away for himself.
I ended up going to Tampa Bay Brewing Company, which had some really good beer, including a seasonal IPA that this avowed hop hater enjoyed and they even had fried pickles, one of my favorite, but hardest to find appetizers.
I picked up a six pack of Jai Alai while I was down there too, but as previously mentioned, most IPA's disgust me (this one did).